John was born in 1962 in Manhattan, New York, to John Millard Gilbert Sr. and Virginia Margaret Raven.

At the age of 15, John began making waves in the world of windsurfing. Competing in the PanAm World Cup, he placed 13th out of 150 of the world’s top windsurfers, most of whom hailed from Europe. Notably, he raced using custom boards he built himself, a skill he developed as a teenager. His talent and determination were evident when he secured third place in the grueling 28-mile race from Kailua to Waikiki, even after his sail ripped. John's mastery of windsurfing continued as he participated in and placed in numerous around-the-island races, often competing against the very best in the world. His sailing adventures took him far out into the Molokai Channel, where he found himself amidst whales—a testament to his adventurous spirit and love for the ocean.

By the age of 21, he had already purchased his first piece of property, and by 24, he had completed a custom home of his own design. His skills as a builder were unparalleled; he founded and grew the largest residential construction company in the Upper Keys, surpassing well-established competitors. His work was recognized for its excellence, with two of his homes being featured in Florida Architecture Magazine before he turned 40. By the age of 30, he had also constructed an office and warehouse on US-1, further cementing his reputation as a leading figure in the construction industry.

At 40, John embraced a new challenge: racing. Despite starting later than most, he quickly made a name for himself, earning Rookie of the Year in Pro 4s open-wheel cars. Competing on some of the toughest tracks, he secured 5th place in Sprint Cars at Hialeah in just his third race. He went on to win his 11th race at Ocala, one of the most challenging tracks, competing against the world’s best drivers. His near-victory at Desoto, where he almost took 2nd place against the legendary David Steel, was a remarkable feat for a rookie Sprint Car driver.

John was a true Renaissance man. His talents extended beyond racing and construction—he built computer estimating programs, painted cars and boats, designed homes, and engineered engines. His ability to design, build, fix, and improve anything he touched was unmatched. He provided his family with a second-to-none lifestyle, loving and supporting them every step of the way.

John spent countless days on the water lobstering, barefoot skiing, wakeboarding, fishing, and often taking his children and their friends out on the boat—even on Christmas Day. The family gathered around the dinner table nearly every evening, fostering a strong and lasting bond. His boisterous laugh and quick wit filled the home with smiles and laughter.

John is survived by his children, Grace Virginia Peil, John Millard Gilbert III, and Candace Faith Hoffman (Korbin); his sister, Karen Anne Gilbert; four grandchildren; two nephews; and his beloved dogs, Mitsou and Katsumi.

Favorite Films

Gladiator (2000) Happy Gilmore (1996) Billy Madison (1995) Little Nicky (2000) Braveheart (1995) The Terminator (1984) Waterworld (1995) The Lawnmower Man (1992) Legally Blonde (2001) Scarface (1983) Joe Dirt (2001) The Best of Chris Farley (1998) Five Summer Stories (1972) Mr. Destiny (1990) How the Grinch Stole Christmas (2000) The Muppet's Christmas Carol (1992) Scrooged (1988) Forrest Gump (1994) Shallow Hal (2001)